The first time she cuts herself free on Penelope's boat.
She's not going back, she tells him, eyes dark-circled and weary. She soothes Aaron, bobbing him gently, and Jack knows it's as much for her benefit as it is for the baby's.
He watches her wait until Sun is on the raft and then carefully hand Aaron over. He watches her hug Hurley and Sayid, holding his breath once she turns to him.
"You're sure you want to do this? We can still make a different plan."
She answers with a crooked smile. "I have to do this."
Penny and Desmond each have an arm wrapped around each other while waving them off. Kate folds her arms over her chest.
Claire Littleton died in childbirth, he maintains when asked. Kate Austen must have died in the crash. He never knew a Kate, he says like he means it. He doesn't recognize her mugshot.
Three years later, in his hospital, John Locke shows up and makes many claims he finds hard to believe. I talked to Kate hurts more than most of them.
The second time she rocks Aaron in her arms as though she's stuck on repeat, each movement automatic and unthinking. When he falls into a peaceful sleep, she tucks him into his makeshift bed and leaves the door ajar on leaving the room.
"I can't go with you, Jack."
He knows why. He knows it by heart but almost can't accept it. He wonders if she'd be as stubborn if Sawyer had stayed on the helicopter with them.
"Then what are you going to do?"
"Same thing I did before the island."
He barely bites back the words running is no way to live, Kate.
"If I go back, I'm going on trial."
He answers with a nod and, to her surprise, doesn't push the issue much more.
In the morning, he tells her he wants to go with her. She exhales an abrupt laugh, surprised, and then stares at him when she realizes he's serious.
They're almost happy. He's halfway content: he spends three years thinking she tastes like the ocean and wanting to protect her at all costs but always tensing his jaw at the sound of sirens and missing what it felt like to help people -- to fix them -- on a regular basis.
Then John finds them, and everything changes.
The third time he notices something dawning on Sawyer's face in the helicopter. It happens in a matter of seconds, and at first it sends genuine relief flooding through him.
Then it chills him, shames him.
When Sawyer leans into Kate and whispers something in her ear, Jack shakes his head.
He was always the leader, whether he liked it or not, and the least he can do is make sure as many people as possible have the chance to leave now.
The last thing he hears before he jumps is Sawyer's startled protest.
He rises from the ocean after a long swim to shore, his chest heaving from the effort, and Juliet is there, a bottle of Dharma rum in her hand. Her eyes are heartbroken, but he thinks she almost smiles at him.
Smoke rises in the distance where the freighter used to be. One of Juliet's hands finds his back; the other presses the rum into his.
The world flashes white, and before the day is over John tells him nobody was supposed to leave.
He can't make himself believe it.
The fourth time he tells Kate to go with Sayid and Miles to get the woman from the freighter, knowing Sawyer would never let anything bad happen to her.
He doesn't see her again until she and Sawyer come crashing through the jungle, worn and dirty, a rifle in Sawyer's hands and Aaron bundled in Kate's arms.
She refuses to get on the helicopter when she has the chance, and it shocks him. He tries to convince her, he argues, he practically demands for her to go. Despite hesitation and visible uncertainty, she resolutely stands her ground.
Sayid, already in and ready to go, is the one to put a firm hand on his shoulder. "She does not want to go."
We do remains unspoken but it hangs in the air, echoed in the wary eyes of Sun and Hurley.
He shakes his head, disbelieving, not wanting to believe. "I'll come back for you."
Kate's lips press together in a crooked smile as she steps back, away from the helicopter, and that smile stays with him for a long time after the island disappears.
Faced with John a few years later, his skepticism hangs by a desperate thread.
The fifth time she's pretty enough standing there, defiant and framed by the lights of the airport, that for a moment he can't say what he wants to.
He had every reason to be upset with her when she kept her secrets, and he knows he took it too far. He knows how far he's fallen since.
She doesn't agree that they made a mistake; she doesn't agree that they weren't supposed to leave. She's furious when he tells her they need to go back.
If he thought they stood a chance of reconciling, her reaction would (does) end that hope.
Even though she eventually changes her mind, nothing goes as planned.
He wanted to save everyone, to make things right, to erase any misery. Instead they discover they're in the 70s, that their friends are living with the Dharma Initiative. Instead Kate is reluctant to go along with his plan. Sayid gets shot, and the bleeding can't be stopped. Juliet disappears down the shaft where the bomb didn't detonate, and Sawyer grieves by turning violent.
His plan crumbles under its own weight; his friends crumble around him.
He doesn't know what he could have done differently, but he would do it if he had another chance.
"Oh." The woman puts her hands up in surprise, bracing herself as she walks out of the lavatory and straight into him. "I'm so sorry."
He smiles politely and excuses himself, oblivious as she deftly hooks the pen in his pocket and hides it between her fingers.
He is a successful spinal surgeon bringing his father's body back to California for a funeral.
She is a caught fugitive being escorted back to the states to stand trial.
He's never eaten an Apollo bar.
She's never owned a New Kids on the Block lunchbox.